- Five 1/3-inch-thick slices of white Pullman bread
- 1 tablespoon plus 1 teaspoon extra-virgin olive oil, plus more for brushing
- 10 pitted prunes
- 1 1/4 cups dry red wine
- One 5-ounce piece of pancetta, cut into 1/4-inch dice
- 4 large garlic cloves, very finely chopped
- 4 ounces vacuum-packed cooked chestnuts, coarsely crumbled
- 1 tablespoon chopped rosemary, plus 2 large sprigs
- 1 tablespoon freshly grated pecorino cheese
- 1/4 teaspoon cayenne pepper
- Salt and freshly ground pepper
- 2 large eggs, lightly beaten
- Two 1 1/4-pound flatiron steaks, each pounded to a 1/3-inch thickness
- 2 1/2 cups beef broth
- 2 large shallots, coarsely chopped
- 2 tablespoons all-purpose flour
- Preheat the oven to 400°. Put the bread on a large baking sheet and brush all over with olive oil. Bake for about 20 minutes, until very crisp and golden brown. Let cool. Break up the toasts and transfer to a food processor. Process to coarse crumbs.
- In a large glass measuring cup, cover the prunes with 1/2 cup of the wine. Microwave at high power for 1 minute, or until the prunes are soft. Cut the prunes into 1/2-inch pieces and transfer to a large bowl along with the soaking wine.
- In a large, deep ovenproof skillet, heat the 1 teaspoon of olive oil. Add one-third of the pancetta and cook over moderate heat until crisp, about 7 minutes. With a slotted spoon, add the pancetta to the prunes. Add the garlic to the skillet and cook over low heat for 1 minute. Scrape the garlic into the bowl. Add the bread crumbs, chestnuts, chopped rosemary, pecorino and cayenne and season with salt and pepper. Stir in the eggs.
- Put the steaks on a work surface and season both sides with salt and pepper. Press half of the stuffing over each steak. Roll up the steaks lengthwise and tie at 2-inch intervals with kitchen string.
- Turn the oven down to 350°. Heat the remaining 1 tablespoon of olive oil in the skillet until shimmering. Add the steaks and cook over moderately high heat until browned all over, about 8 minutes. Turn the steaks seam side down. Add the remaining 3/4 cup of wine and pancetta to the skillet along with the broth, rosemary sprigs and shallots; bring to a boil. Transfer the skillet to the oven and braise the steaks for about 25 minutes, turning once, until a thermometer inserted in the steaks registers 130° for medium-rare to medium meat.
- Transfer the steaks to a carving board to rest for 5 minutes. Whisk the flour into the pan juices and simmer over moderately high heat, whisking a few times, until the gravy is thickened and slightly reduced, about 3 minutes. Strain the gravy into a small saucepan, pressing on the solids. Season with salt and pepper and keep the gravy warm.
- Untie the steaks and slice crosswise 1/4 inch thick. Serve with the gravy.
Thanks to warm days and cool nights, Amador County reds develop concentrated flavors without becoming overly jammy or syrupy, making them perfect for this elegant steak. The Sobon family has championed this style since the '70s. Look for its Syrah or Zinfandel.